Iodine → 6-Chloro-2-iodopyridin-3-amine

HRID 513063

反応式

HRID 513063 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[I:9]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[Cl:1][C:2]1[N:7]=[C:6]([I:9])[C:5]([NH2:8])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 807IodineHCID 793055-Amino-2-chloropyridine

生成物 1

HCID 184070436-Chloro-2-iodopyridin-3-amine収率 86.4%

試薬・触媒・溶媒 2

HCID 159865Silver sulfate触媒HCID 702Ethanol溶媒

反応条件

温度
20 °C

実験手順

To a solution of 6-chloro-pyridin-3-ylamine (10.0 g, 77.8 mmol) in EtOH (150 mL) was added Ag2SO4 (12.1 g, 38.9 mmol) and I2 (23.7 g, 93.4 mmol) at room temperature. The mixture was stirred at 20° C. overnight. The solvent was removed by evaporation under vacuum. Water (100 mL) and EtOAc (200 mL) were added to the residue. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1) to give 6-chloro-2-iodo-pyridin-3-ylamine (17.1 g, 86%). 1H NMR (DMSO, 300 MHz) δ 7.16 (d, J=8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 5.57 (s, 2H).

後処理

  1. customThe solvent was removed by evaporation under vacuum
  2. additionWater (100 mL) and EtOAc (200 mL) were added to the residue
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customto give the crude product, which
  8. customwas purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1)

出典と根拠

ORDレコード
ord-df791a2e39074c7ca9e7896999ccfcac
出典データセット
uspto-grants-2015_08
特許番号
US09102672B2

関連ノート

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